Cleavage of Oximes, Semicarbazones, and Phenylhydrazones with Supported Potassium Permanganate

Ahmad Shaabani; Soheila Naderi; Abbas Rahmati; Zahra Badri; Maria Darvishi; Donald G. Lee

doi:10.1055/s-2005-916027

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2005(18): 3023-3025
DOI: 10.1055/s-2005-916027

SHORTPAPER

Cleavage of Oximes, Semicarbazones, and Phenylhydrazones with Supported Potassium Permanganate

Ahmad Shaabani*^a, Soheila Naderi^a, Abbas Rahmati^a, Zahra Badri^a, Maria Darvishi^a, Donald G. Lee^b
^a Department of Chemistry, Shahid Beheshti University, P.O. Box 19839-4716, Tehran, Iran
^b Department of Chemistry and Biochemistry, University of Regina, SK S4S 0A2, Canada
Fax: +98(21)2403041; e-Mail: a-shaabani@cc.sbu.ac.ir;

Further Information

Publication History

Received 25 May 2005
Publication Date:
16 September 2005 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Potassium permanganate supported on manganese(II) sulfate or activated manganese dioxide can be used effectively for the oxidative cleavage of oximes and semicarbazones under solvent-free conditions and for the cleavage of phenylhydrazones in dichloromethane. The residue that remains after extraction of the organic products, primarily manganese oxides, can be recycled, making the process, in theory, infinitely sustainable.

Key words

oximes - semicarbazones - phenylhydrazones - potassium permanganate

References

1 Green TW. Wuts PG. Protective Groups in Organic Synthesis 3rd ed.: John Wiley and Sons; New York: 1991.

Google Scholar
2 Corsaro A. Chiacchio U. Pistara V. Synthesis 2001, 1903

Article in Thieme Connect Google Scholar
3 Barton DHR. Beaton JM. J. Am. Chem. Soc. 1961, 83: 4083

Crossref Google Scholar
4 Kadzyauskas PP. Zefirov NS. Russ. Chem. Rev. (Engl. Transl.) 1968, 37: 543

Crossref Google Scholar
5 Mukai C. Hanaoka M. Synlett 1996, 11

Article in Thieme Connect Google Scholar
6 Czekelius C. Carreira EM. Angew. Chem. Int. Ed. 2005, 44: 612

Crossref Google Scholar
7a Solid Supports and Catalysts in Organic Synthesis Smith K. Ellis Harwood and PTR Prentice Hall; New York: 1992.

Google Scholar
7b Laszlo P. In Comprehensive Organic Synthesis Vol. 7: Trost BM. Pergamon; New York: 1992. p.893

Google Scholar
8 Shaabani A. Lee DG. Recent Res. Dev. Org. Chem. 2003, 85

Google Scholar
9 Chrisman W. Blankinship M. Taylor B. Harris CE. Tetrahedron Lett. 2001, 42: 4775

Crossref Google Scholar
10 Hajipour AR. Adibi H. Ruoho AE. J. Org. Chem. 2003, 68: 4553

Crossref Google Scholar
11 Jadhav VK. Wadgaonkar PP. Joshi PL. Salunkhe MM. Synth. Commun. 1999, 29: 1989

Crossref Google Scholar
12 Mohammadpoor-Baltork I. Khodaei MM. Hajipour AR. Aslani E. Monatsh. Chem. 2003, 134: 539

Crossref Google Scholar
13 Singh N. Lee DG. Org. Process Res. Dev. 2001, 5: 599

Crossref Google Scholar
14 Shaabani A. Mirzaei P. Lee DG. Catal. Lett. 2004, 97: 119

Crossref Google Scholar
15 Shaabani A. Mirzaei P. Naderi S. Lee DG. Tetrahedron 2004, 60: 11415

Crossref Google Scholar
16 Alexander EA. Tompkins FC. Trans. Faraday Soc. 1939, 35: 1156

Crossref Google Scholar
17 Kolthoff IM. Sandell EB. Textbook of Quantitative Inorganic Analysis MacMillan; New York: 1955. p.565

Google Scholar
18 Arndt D. Manganese Compounds as Oxidizing Agents in Organic Chemistry Open Court; La Salle: 1981. Chap. 1.

Google Scholar
19 Shinada T. Yoshihara K. Tetrahedron Lett. 1995, 36: 6701

Crossref Google Scholar